Réaction #1726684

Équation de réaction

methanesulfonyl chloride

2B

(5-(4-Chlorophenyl)-1,3,4-oxadiazol-2-yl)(3-hydroxyazetidin-1-yl)methanone

methyl 5-(4-chlorophenyl)-1,3,4-oxadiazole-2-carboxylate

Triethylamine

→

2C

Rendement 75.0%

1-(5-(4-Chlorophenyl)-1,3,4-oxadiazole-2-carbonyl)azetidin-3-yl methanesulfonate

Rendement 75.0%

Solvants

dichloromethane

Conditions de réaction

Traitement

1. 1
   Températurewas cooled in an ice-bath
2. 2
   workup.ADDITIONAfter the addition
3. 3
   Autrethe cooling bath was removed
4. 4
   AutreThe reaction mixture was transferred to a reparatory funnel
5. 5
   Lavagewas washed with water
6. 6
   AutreThe organic solution was dried (phase separator)
7. 7
   Autreevaporated
8. 8
   workup.ADDITIONDichloromethane (50 mL) and diethyl ether (200 mL) were added
9. 9
   Filtrationthe solid product was collected by filtration
10. 10
    LavageThe solid was washed twice with diethyl ether
11. 11
    Autredried in vacuo
12. 12
    AutreThe product was purified
13. 13
    Lavagefirst eluting with dichloromethane
14. 14
    workup.ADDITIONwith a mixture of dichloromethane and methanol containing 2M NH3 (20:1)

Mode opératoire

A suspension of 2B —which contained approximately 50% of methyl 5-(4-chlorophenyl)-1,3,4-oxadiazole-2-carboxylate as an impurity—(1.38 g, 2.47 mmol) in dichloromethane (50 mL) was cooled in an ice-bath. Triethylamine (0.51 mL, 3.70 mmol) was added followed by methanesulfonyl chloride (0.27 mL, 3.45 mmol). After the addition, the cooling bath was removed. The mixture was stirred for 7 h. The reaction mixture was transferred to a reparatory funnel and was washed with water followed by aqueous NaHCO3. The organic solution was dried (phase separator) and evaporated. Dichloromethane (50 mL) and diethyl ether (200 mL) were added and the solid product was collected by filtration. The solid was washed twice with diethyl ether and then dried in vacuo. The product was purified using flash column chromatography first eluting with dichloromethane and then with a mixture of dichloromethane and methanol containing 2M NH3 (20:1). There was obtained 0.66 g (75%) of 2C as a solid. 1H NMR (500 MHz, CDCl3): δ 3.13 (s, 3H), 4.43 (dd, 1H), 4.65 (dd, 1H), 4.87 (dd, 1H), 5.12 (dd, 1H), 5.41 (m, 1H), 7.53 (d, 2H), 8.10 (d, 2H), MS (APCI+) m/z 358 [M+H]+.

Source